Aryl sulfimides



P 2,891,979 Patented June 23, v1959 ARYL SULFIMIDES No Drawing. Application July 1, 1957 Serial No. 668,929 ,1

2 Claims. (Cl. 260-439) 2 A fine white crystalline precipitate was formed. This was filtered ofi at 35 C. and dried. The yield was 25 grams which is a 76.8% yield. The melting point of the product was 229-234 C. In order to further purify the product it wasdissolved in one liter of water and brought to a boil. The pH was adjusted to 7.0 with sodium carbonate whereupon all the material went into solution. The solution was carbon treated with activated carbon and filtered. The filtrate was acidified with sufiicient acid to make the solution 5% HCl, this addition being made at 50- 60 C. dropwise. A fine white crystalline precipitate was formed and separated by filtration at 35 C. This precipitate was dried at 40-50 C. and yielded 17 grams of products, a yield of 52.2% of theoretical. The

This invention relates to long-chain aryl sulfimides conmelting point was 233-238 C., the formula being taining two disulfimide groups, substitution products thereof and salts of the foregoing.

This application is a continuation-in-part of our copending application Serial No. 615,012, filed October 10, 1956, now Patent No. 2,848,392.

In accordance with the present invention, we provide novel compounds which we may utilize in the nickel plating process, such additives being of the following general formula:

Other examples of compounds according to the invention may be produced in the same way, for example, the compounds appearing in Table I.

Table I The foregoing are but a few examples of the numerous similar compounds within scope of the above stated general formula and which may be made in the same way as the example shown above by selection of suitable starting materials, all of which will be obvious from the foregoing to persons skilled in the art. Preferred compounds are of the formula @somnsmQo on,orno ..somusoi tives in nickel electrodeposition, we believe that they are undoubtedly useful for other purposes.

These compounds may be synthesized by reacting together aryl sulfonamides with compounds of the general formula ClSO C H O[CH CH O],,C H SO Cl wherein n is an integer from 1 to 2.

A specific example of a compound according to the invention was synthesized as follows:

A quantity of 0.05 mol (20.5 grams) of 1,2-diphenoxyethane-p,p'-disulfonyl chloride was added to 0.2 mol (31.4 grams) of benzene sulfonamide dissolved in 0.2 mol (8.34 grams, 96% strength) of NaOH in 150 cc. of water. The sulfonyl chloride was added to the sulfonamide solution over a period of one-half hour at from 50 to 55 C. The reaction mixture was stirred for one-half hour at this temperature and then heated to reflux for 1 hour. The mixture was allowed to stand overnight and diluted to '600 cc. The pH was adjusted to 2.5 with dilute hydrochloric acid. The excess benzene sulfonamide was filtered ofi at 20 C. It amounted to 3 grams. The filtrate, a clear straw-colored solution was acidified with hydrochloric acid by the addition of enough to make the solution 5% H01, this addition being made at 5060 C.

where n is an integer from 1 to 2 or salts thereof or derivatives of said compounds or said salts wherein from 1 to 4 nuclear hydrogens are replaced by radicals of the class consisting of chlorine, bromine, fluorine, methyl, ethyl, ca-rboxyl and sulfamyl. Compounds so prepared within the above indicated class of compounds are suitable as additives for use in electrodeposition of nickel of improved lustre when used either as the sole brightening additive or with auxiliary brightening additives capable of enhancing the brilliance of the deposit. When such compounds are used as the sole brightening additives, the solutions under all normal circumstances are capable of producing deposits of improved lustre and in some instances are capable of producing better than semi-bright deposits and even deposits of image reflecting brightness under favorable conditions. Still brighter deposits can be produced by the addition of auxiliary brighteners.

It will be understood that the substitution products shown in Table I may be made by a procedure exactly as described in the example except that instead of using benzene sulttonamide, a substituted benzene sulfonamide would be used. The proportions of such substituted ben zene sulfonamide preferably would be molecularly equiva- 33 l lent to the quantity of benzene sulfonamide used in the and derivatives of the foregoing wherein from 1 to 4 nuabove example. The salts may be produced by reaction clear hydrogen atoms are replaced by radicals of the class with, for example, the hydroxide of the metal whose salt consisting of chlorine, bromine, fluorine, methyl, ethyl, is desired. Sodium, potassium, nickel, iron and cobalt carboxyl and sulfamyl. salts are examples of salts contemplated by the invention. 5 2. As a new composition of matter, a compound of the Other soluble metal salts can be produced similarly. formula @somnsmQoomomoQsomnsoQ Having thus described the invention, what is claimed is: and the sodium, potassium, iron, cobalt and nickel salts 1. As new compositions of matter compounds of the thereof and derivatives of the foregoing wherein from general formula 1 to 4 nuclear hydrogen atoms are replaced by radicals wherein n is an integer from 1 to 2 inclusive, and the of the class consisting of chlorine, bromine, fluorine, sodium, potassium, iron, cobalt and nickel salts thereof methyl, ethyl, carboxyl and sulfamyl.

References Cited in the file of this patent UNITED STATES PATENTS 2,309,870 Salomon Feb. 2, 1943 OTHER REFERENCES Richter: Textbook of Organic Chemistry, 1952, pages 256 and 257. 

1. AS NEW COMPOSITIONS OF MATTER COMPOUNDS OF THE GENERAL FORMULA 